Luxury rentals in Chicago

Find and book unique accommodation on Airbnb

Top-rated luxury holiday rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1

Luxe

Home in Highland Park

Champions Point Legendary Living

Live like a legend at 2700 Point Ln! This estate was built with privacy, security, and luxury in mind - a private oasis on 7.39 acres surrounded by mature pines, fenced and gated. Enjoy putting on your professional grade putting green, fishing in your private pond stocked with bass and bluegill, and swimming in your zero-entry infinity edge pool! Inside enjoy your movie theatre, commercial gym, cigar lounge, wine cellar, pool tables, bars, salon, salt water aquariums, and full basketball court!

Luxe

The spacious living area features a dining table with black chairs and a wooden tabletop, complemented by an inviting lounge area with a large sofa and accent chairs. Large windows allow natural light to illuminate the room, enhancing its modern design.

Flat in Gold Coast

4.88 out of 5 average rating, 33 reviews

Luxury Designer Penthouse|Private Deck|Gold Coast

BRAND NEW PENTHOUSE IN THE HEART OF GOLD COAST! Enjoy your own penthouse in Chicago's Gold Coast-the city's center of nightlife, restaurants, and shopping. In a completely redeveloped luxury brownstone, your 3 bedroom/3 bathroom penthouse offers ultra high-end appliances, design, and finishes, with two private patios/decks (truly unique amenity in Chicago) and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between!

Luxe

A spacious living area is featured, showcasing a modern sectional sofa adorned with cushions. A wooden coffee table sits centrally, accompanied by decorative items. The open layout includes a dining area with circular chairs and a large window allowing natural light to fill the room.

Apartment in Uptown

5 out of 5 average rating, 9 reviews

Ultra Modern Luxury - New Construction 4 Bedrooms

🌟 New 4BR Duplex in Uptown/Edgewater! 🌟 This ultra-modern 2500+ SF duplex is steps from Lake Michigan, Andersonville, and vibrant dining, shopping, & nightlife. Featuring 4 bedrooms and 2.5 baths, the condo boasts a private rooftop deck with a fire pit 🔥, loungers, and patio seating. Just ½ block to the Red Line 🚇. Garage parking included. Concierge services available. Ideal for short-term stays, executives, or insurance clients. Enjoy comfort & convenience! ✨

Luxe

Flat in Chicago Loop

4.73 out of 5 average rating, 11 reviews

PH w/ Bean & Lake Views, An Elite Stay

For travelers with uncompromising standards, 'The Orion' is an exclusive 3000ft² penthouse offering iconic The Bean & Millennium Park views and access to a private amenity floor. It's a proven elite experience, with a remarkable 9 out of 10 recent guests leaving a 5-star review.

Luxe

A spacious living area is showcased, featuring a modern sectional sofa with neutral tones. A sleek kitchen island, equipped with high-end appliances, complements a dining table surrounded by colorful chairs. Large windows allow ample natural light and provide views of the city beyond.

Flat in Chicago Loop

4.79 out of 5 average rating, 24 reviews

Luxury Downtown 4BR | Exclusive Design PH

Discover a premier Chicago experience in this luxury penthouse, ideal for travelers who value amazing views and a stylish stay. Our guest reviews prove it, with a 94% 5-star rating since 2023 for our stunning views and spotless cleanliness.